Glucuronidation of nicotine and cotinine by UGT2B10: Loss of function by the UGT2B10 codon 67 (Asp>Tyr) polymorphism

Cancer Research

Volumn 67, Issue 19, 2007, Pages 9024-9029

  Chen, Gang ^a   Blevins Primeau, Andrea S ^a   Dellinger, Ryan W ^a   Muscat, Joshua E ^a   Lazarus, Philip ^a  

^a PENN STATE COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COTININE; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 2B10; NICOTINE; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN HEK293; CODON; CONTROLLED STUDY; GENE; GENE FUNCTION; GENETIC POLYMORPHISM; GENOTYPE; GLUCURONIDATION; HUMAN; HUMAN CELL; HUMAN TISSUE; LIVER MICROSOME; PRIORITY JOURNAL; SMOKING; TOBACCO; UGT2B10 GENE; WILD TYPE;

CELL LINE; CODON; COTININE; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; ISOENZYMES; KINETICS; MICROSOMES, LIVER; NICOTINE; POLYMORPHISM, GENETIC;

EID: 35148893148     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-07-2245     Document Type: Article

References (20)

1. Hukkanen J, Jacob P III, Benowitz NL. Metabolism and disposition kinetics of nicotine. Pharmacol Rev 2005;57:79-115.
2. Caldwell WS, Greene JM, Byrd GD, et al. Characterization of the glucuronide conjugate of cotinine: a previously unidentified major metabolite of nicotine in smokers' urine. Chem Res Toxicol 1992;5:280-5.
3. Byrd GD, Uhrig MS, deBethizy JD, et al. Direct determination of cotinine-N-glucuronide in urine using thermospray liquid chromatography/mass spectrometry. Biol Mass Spectrom 1994;23:103-7.
4. Byrd GD, Caldwell WS, Bhatti BS, Ravard A, Crooks PA. Determination of nicotine N-1-glucuronide, a quaternary N-glucuronide conjugate, in human biological samples. Drug Metabol Drug Interact 2000;16:281-97.
5. Ghosheh O, Vashishtha SC, Hawes EM. Formation of the quaternary ammonium-linked glucuronide of nicotine in human liver microsomes: identification and stereoselectivity in the kinetics. Drug Metab Dispos 2001;29:1525-8.
6. Kuehl GE, Murphy SE. N-glucuronidation of trans-3′- hydroxycotinine by human liver microsomes. Chem Res Toxicol 2003;16:1502-6.
7. Benowitz NL, Jacob P III, Fong I, Gupta S. Nicotine metabolic profile in man: comparison of cigarette smoking and transdermal nicotine. J Pharmacol Exp Ther 1994;268:296-303.
8. Kuehl GE, Murphy SE. N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP- glucuronosyltransferases. Drug Metab Dispos 2003;31:1361-8.
9. Ghosheh O, Hawes EM. N-glucuronidation of nicotine and cotinine in human: formation of cotinine glucuronide in liver microsomes and lack of catalysis by 10 examined UDP-glucuronosyltransferases. Drug Metab Dispos 2002;30:991-6.
10. Nakajima M, Tanaka E, Kwon JT, Yokoi T. Characterization of nicotine and cotinine N-glucuronidations in human liver microsomes. Drug Metab Dispos 2002;30:1484-90.
11. Wiener D, Fang JL, Dossett N, Lazarus P. Correlation between UDP-glucuronosyltransferase genotypes and 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone glucuronidation phenotype in human liver microsomes. Cancer Res 2004;64:1190-6.
12. 14C]-glucuronic acid. Anal Biochem 1986;159:198-205.
13. Sun D, Chen G, Dellinger RW, Duncan K, Fang JL, Lazarus P. Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants. Breast Cancer Res 2006;8:R50.
14. Upadhyaya P, Kenney PM, Hochalter JB, Wang M, Hecht SS. Tumorigenicity and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol enantiomers and metabolites in the A/J mouse. Carcinogenesis 1999;20:1577-82.
15. Gallagher CJ, Muscat JE, Hicks AN, et al. The UDP-glucuronosyltransferase 2B17 gene deletion polymorphism: sex-specific association with urinary 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronidation phenotype and risk for lung cancer. Cancer Epidemiol Biomarkers Prev 2007;16:823-8.
16. Nishimura M, Naito S. Tissue-specific mRNA expression profiles of human phase I metabolizing enzymes except for cytochrome P450 and phase II metabolizing enzymes. Drug Metab Pharmacokinet 2006;21:357-74.
17. Dellinger RW, Fang JL, Chen G, Weinberg R, Lazarus P. Importance of UDP-glucuronosyltransferase 1A10 (UGT1A10) in the detoxification of polycyclic aromatic hydrocarbons: decreased glucuronidative activity of the UGT1A10139Lys isoform. Drug Metab Dispos 2006;34:943-9.
18. Benowitz NL, Jacob P III. Metabolism of nicotine to cotinine studied by a dual stable isotope method. Clin Pharmacol Ther 1994;56:483-93.
19. Malaiyandi V, Sellers EM, Tyndale RF. Implications of CYP2A6 genetic variation for smoking behaviors and nicotine dependence. Clin Pharmacol Ther 2005;77:145-58.
20. Nakajima M, Yokoi T. Interindividual variability in nicotine metabolism: C-oxidation and glucuronidation. Drug Metab Pharmacokinet 2005;20:227-35.